Airbnb Properties for Sale in Chestertown, MD

Looking for a vacation rental investment in Chestertown, MD with high ROI ?

Explore a range of newly added short-term rental homes in Chestertown, MD. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Chestertown, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
107 MALONE Avenue CHESTERTOWN, MD Welcome to 107 Malone Ave. in the friendly community of Foxley Manor....A Great place to c...	3 beds \| 1 baths \| 1,200 sq.ft.	$290,000	Airbnb cash on cash: 5.73% Traditional cash on cash: 4.96% Airbnb Rental Income: $2892 Traditional Rental Income: $2012 Airbnb ROI: 5.73% Traditional ROI: 4.96%
109 S COLLEGE Avenue CHESTERTOWN, MD Charming Move-In Ready Colonial in the Heart of Town This beautifully updated Colonial ble...	3 beds \| 3 baths \| 1,216 sq.ft.	$449,900	Airbnb cash on cash: 3.43% Traditional cash on cash: 2.44% Airbnb Rental Income: $2892 Traditional Rental Income: $1802 Airbnb ROI: 3.43% Traditional ROI: 2.44%
23110 OLD FAIRLEE Road CHESTERTOWN, MD Turnkey Perfection! Fully Renovated Ranch Home in Desirable Fairlee! Prepare to be impress...	3 beds \| 1 baths \| 1,805 sq.ft.	$349,900	Airbnb cash on cash: 4.93% Traditional cash on cash: 3.62% Airbnb Rental Income: $2892 Traditional Rental Income: $1791 Airbnb ROI: 4.93% Traditional ROI: 3.62%
103 METCALF RD CHESTERTOWN, MD Brand new home in Historic Chestertown available for move-in this October. This home featu...	3 beds \| 2 baths \| 1,280 sq.ft.	$259,900	Airbnb cash on cash: 6.6% Traditional cash on cash: 6.24% Airbnb Rental Income: $2892 Traditional Rental Income: $2133 Airbnb ROI: 6.6% Traditional ROI: 6.24%
318 LINCOLN CHESTERTOWN, MD Kent County welcomes you with a move-in ready home that's full of updates! This 3-bedroom,...	3 beds \| 2 baths \| 960 sq.ft.	$269,000	Airbnb cash on cash: 6.41% Traditional cash on cash: 6.29% Airbnb Rental Income: $2892 Traditional Rental Income: $2190 Airbnb ROI: 6.41% Traditional ROI: 6.29%
7521 PINE Avenue CHESTERTOWN, MD Priced to sell! This 3-bedroom, 1-bath rancher in Quaker Estates offers convenient living ...	3 beds \| 1 baths \| 1,040 sq.ft.	$250,000	Airbnb cash on cash: 7.34% Traditional cash on cash: 6.62% Airbnb Rental Income: $2892 Traditional Rental Income: $2051 Airbnb ROI: 7.34% Traditional ROI: 6.62%

Vacation Rentals in Chestertown

There are 6 vacation rental properties available for sale in the city of Chestertown . The median list price of Airbnb properties available for sale in Chestertown is $370,000 and the average price per square foot is $172. The cash on cash return on vacation rentals in Chestertown is 1.00%. The average monthly short term rental income in Chestertown is $1,999.

Chestertown, MD Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 6 Airbnb properties available for sale in Chestertown.

In 2025, the best neighborhood to buy short term rental property is CHESTERTOWN.

In December 2025, the average Airbnb occupancy rate in Chestertown is 28%.

Airbnb data on vacation rentals in Chestertown, MD is available at Mashvisor. You can access data such as listings, real-time pricing trends, Chestertown, MD market insights, guest information and booking details, seasonality trends and historical Chestertown, MD Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Chestertown, MD

107 MALONE Avenue

CHESTERTOWN, MD

3 beds | 1 baths | 1,200 sq.ft.

$290,000

Airbnb cash on cash: 5.73%

Traditional cash on cash: 4.96%

Airbnb Rental Income: $2892

Traditional Rental Income: $2012

Airbnb ROI: 5.73%

Traditional ROI: 4.96%

109 S COLLEGE Avenue

CHESTERTOWN, MD

3 beds | 3 baths | 1,216 sq.ft.

$449,900

Airbnb cash on cash: 3.43%

Traditional cash on cash: 2.44%

Airbnb Rental Income: $2892

Traditional Rental Income: $1802

Airbnb ROI: 3.43%

Traditional ROI: 2.44%

23110 OLD FAIRLEE Road

CHESTERTOWN, MD

3 beds | 1 baths | 1,805 sq.ft.

$349,900

Airbnb cash on cash: 4.93%

Traditional cash on cash: 3.62%

Airbnb Rental Income: $2892

Traditional Rental Income: $1791

Airbnb ROI: 4.93%

Traditional ROI: 3.62%

103 METCALF RD

CHESTERTOWN, MD

3 beds | 2 baths | 1,280 sq.ft.

$259,900

Airbnb cash on cash: 6.6%

Traditional cash on cash: 6.24%

Airbnb Rental Income: $2892

Traditional Rental Income: $2133

Airbnb ROI: 6.6%

Traditional ROI: 6.24%

318 LINCOLN

CHESTERTOWN, MD

3 beds | 2 baths | 960 sq.ft.

$269,000

Airbnb cash on cash: 6.41%

Traditional cash on cash: 6.29%

Airbnb Rental Income: $2892

Traditional Rental Income: $2190

Airbnb ROI: 6.41%

Traditional ROI: 6.29%

7521 PINE Avenue

CHESTERTOWN, MD

3 beds | 1 baths | 1,040 sq.ft.

$250,000

Airbnb cash on cash: 7.34%

Traditional cash on cash: 6.62%

Airbnb Rental Income: $2892

Traditional Rental Income: $2051

Airbnb ROI: 7.34%

Traditional ROI: 6.62%

Vacation Rentals in Chestertown

Chestertown, MD Short Term Rentals FAQs for Buyers, Sellers and Investors

How many Airbnb properties are available for sale in Chestertown?

Which neighborhoods in Chestertown to invest in 2025 for short term rentals?

What is the average Airbnb occupancy rate in Chestertown, MD?

How to get Chestertown, MD Airbnb data?

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